Hydrochloric Acid → HCID 58104603, Verbindung

HRID 588003

Reaktionsgleichung

Reaktionsgleichung von HRID 588003
C(OC([N:8]1[CH2:12][CH2:11][C@H:10]([C@H:13]([OH:19])[CH:14]([CH2:17][CH3:18])[CH2:15][CH3:16])[CH2:9]1)=O)(C)(C)C.CN(C=O)C.[H-].[Na+].[Cl:27][C:28]1[CH:33]=[CH:32][CH:31]=[C:30](F)[C:29]=1[Cl:35].Cl.CCO>>[Cl:27][C:28]1[C:29]([Cl:35])=[CH:30][CH:31]=[CH:32][C:33]=1[O:19][C@@H:13]([C@H:10]1[CH2:11][CH2:12][NH:8][CH2:9]1)[CH:14]([CH2:15][CH3:16])[CH2:17][CH3:18]

Komponenten

7

Edukt 6

HCID 313Hydrochloric AcidHCID 702EthanolHCID 6228DimethylformamideHCID 24758Sodium hydride2×HCID 119011Benzene, 1,2-dichloro-3-fluoro-HCID 58104618(S)-3-((R)-2-Ethyl-1-hydroxybutyl)pyrrolidine-1-carboxylic Acid t-Butyl Ester

Produkt 1

HCID 58104603HCID 58104603, Verbindung

Versuchsvorschrift

(S)-3-((R)-2-Ethyl-1-hydroxybutyl)pyrrolidine-1-carboxylic acid t-butyl ester (28 mg, 0.1 mmol) was dissolved in DMF (380 μL, 4.9 mmol). 60% Sodium hydride in oil (0.4:0.6, sodium hydride:mineral oil, 18.6 mg, 310 μmol) was slowly added, and the resulting mixture was stirred at room temperature for 15 minutes. 1,2-Dichloro-3-fluorobenzene (23.8 μL, 206 μmol) was added and the mixture was stirred at 70° C. for 3 hours. The mixture was concentrated, treated with 1.25M HCl in EtOH (578 μL, 722 μmol), then stirred overnight at room temperature. The product was concentrated under vacuum, redissolved in 1:1AcOH:H2O, filtered, and purified by preparative HPLC to yield the title compound as a mono-TFA salt (5.3 mg, 97% purity). MS m/z: [M+H] calcd for C16H23Cl2NO, 316.12. found 316.3.

Aufarbeitung

  1. stirringthe mixture was stirred at 70° C. for 3 hours
  2. concentrationThe mixture was concentrated
  3. stirringstirred overnight at room temperature
  4. concentrationThe product was concentrated under vacuum
  5. dissolutionredissolved in 1:1AcOH
  6. filtrationH2O, filtered
  7. custompurified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-2f62fac8d9f540fc87401aef921c71d2
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09227933B2

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